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3-Acetamidoadamantane-1-carboxylic acid

Acta Cryst. (2006). E62, o5406–o5408 [doi:10.1107/S1600536806045417]

[acetamidoadamantane]A and B molecules of 3-acetamido-1-adamantane-
carboxylic acid related by a pseudo-inversion centre. Hydrogen bonds are depicted as dotted lines.
The title compound is an intermediate in the preparation of an unnatural amino acid, 3-amino-1-adamantane carboxylic
acid. It crystallises in a monoclinic space group with two molecules per asymmetric unit, A and B, related by a pseudoinversion centre. The intermolecular O-H···O hydrogen bonds link the symmetry-related molecules into infinite chains of A and B molecules parallel to the [101] direction. The intermolecular N-H···O hydrogen bonds cross-link these two chains whereas adamantyl cages create a hydrophobic surface around them.
K. Molčanov, B. Kojic-Prodic, N. Basaric and K. Mlinaric-Majerski